EP0743994B1 - Anthraquinone dyes containing a fluorosulphonyl group and use thereof - Google Patents

Anthraquinone dyes containing a fluorosulphonyl group and use thereof Download PDF

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Publication number
EP0743994B1
EP0743994B1 EP95907057A EP95907057A EP0743994B1 EP 0743994 B1 EP0743994 B1 EP 0743994B1 EP 95907057 A EP95907057 A EP 95907057A EP 95907057 A EP95907057 A EP 95907057A EP 0743994 B1 EP0743994 B1 EP 0743994B1
Authority
EP
European Patent Office
Prior art keywords
compound
formula
parts
aromatic polyester
plastics
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP95907057A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0743994A1 (en
Inventor
Nigel Hall
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dystar Textilfarben GmbH and Co Deutschland KG
Original Assignee
Dystar Textilfarben GmbH and Co Deutschland KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dystar Textilfarben GmbH and Co Deutschland KG filed Critical Dystar Textilfarben GmbH and Co Deutschland KG
Publication of EP0743994A1 publication Critical patent/EP0743994A1/en
Application granted granted Critical
Publication of EP0743994B1 publication Critical patent/EP0743994B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive groups
    • C09B62/80—Anthracene dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/56—Mercapto-anthraquinones
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/70—Material containing nitrile groups
    • D06P3/72—Material containing nitrile groups using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/79—Polyolefins
    • D06P3/794—Polyolefins using dispersed dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8228—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
    • D06P3/8233—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • the present invention relates to a process for colouring aromatic polyester textile materials, to a process for the mass coloration of plastics and to certain novel anthraquinone dyes.
  • JP-A-54-050681 discloses dyes, including anthraquinone dyes for use as reactive disperse dyes for cellulose.
  • US-A-3952029 discloses the use of certain anthraquinone dyes for use in the colouration of nylon fibres.
  • a process for colouring an aromatic polyester textile material or fibre blend thereof which comprises applying to the aromatic polyester textile material or fibre blend thereof which comprises applying to the aromatic polyester textile material a compound of Formula (1) or (2):
  • the compounds of Formulae (1) and (2) may be mixed or the compounds of Formulae (1) and (2) may be mixed with dyes which do not contain an -SO 2 F group; such mixtures are a feature of the present invention.
  • the mixtures may be simple physical mixtures or may be mixed crystals formed for example by co-crystallisation. Such mixtures generally show improvement in dyeing properties. Crystalline modifications of compounds of Formula (1) exist and the present definition includes such crystalline modifications which may for example be formed by heat treatment.
  • the presence of one or more -SO 2 F groups in a dye molecule generally improves the properties of that dye and confers surprisingly good wet-fastness and lightfastness properties.
  • the synthetic textile material is an aromatic polyester, especially polyethylene terephthalate.
  • Fibre blends may comprise mixtures of different synthetic textile materials, which may be selected from secondary cellulose acetate, cellulose triacetate, polyamide, polyacrylonitrile and natural textile materials and the aromatic polyester.
  • Preferred fibre blends are those of polyester-cellulose such as polyester-cotton.
  • the textile materials or blends thereof may be in the form of filaments, loose fibres, yarn, woven or knitted fibres.
  • the dyes of Formulae (1) and (2) have low solubility in water, being free from water solubilising groups such as -SO 3 H, -CO 2 H, PO 3 H and quaternary amino.
  • the dye of of Formula (1) or (2) may be applied to the aromatic polyester textile materials or fibre blends thereof by methods which are conventionally employed in dyeing such materials and fibre blends with disperse dyes.
  • the dye of Formula (1) or (2), in the form of an aqueous dispersion may be applied by dyeing, padding or printing processes using the conditions and additives conventionally used in carrying out such processes.
  • the process conditions may be selected from the following:
  • the compound of Formula (1) or (2) is applied as a dispersion comprising from 0.001% to 4% of the compound in aqueous medium.
  • the present compounds generally provide coloured textile material which shows good fastness to washing, light and heat.
  • compositions comprising dispersions of the compound of Formula (1) or (2) are novel and form a further feature of the present invention.
  • the compositions typically comprise from 1% to 30% of the compound of Formula (1) or (2) and are preferably buffered at a pH from 2 to 7, more preferably at a pH from 4 to 6.
  • dispersions may further comprise ingredients conventionally used in dyeing applications such as dispersing agents, for example lignosulphonates, naphthalene sulphonic acid/formaldehyde condensates or phenol/cresol/sulphanilic acid/formaldehyde condensates, surfactants, wetting agents such as alkyl aryl ethoxylates which may be sulphonated or phosphated, inorganic salts, de-foamers such as mineral oil or nonanol, organic liquids and buffers.
  • Dispersing agents may be present at from 10% to 200% on the weight of the compound of Formula (1) or (2).
  • Wetting agents may be used at from 0% to 20% on the weight of the compound of the Formula (1) or (2).
  • the dispersions may be prepared by bead milling the compound of Formula (1) or (2) with glass beads or sand in an aqueous medium.
  • a process for the mass colouration of plastics which comprises incorporating into a plastics material a compound or mixture, which is free from water solubilising groups, containing a compound of Formula (1) or (2).
  • the plastics may be selected from polystyrene, acrylics, stryene/acrylonitrile mixtures, acrylonitrile/butadiene/styrene mixtures, polycarbonate, polyether-sulphone, nylons, rigid PVC (uPVC) and polypropylene.
  • the compound may be incorporated by blending with granules or powdered plastics material by, for example, dry tumbling or high-speed mixing followed by injection moulding on a screw machine or by conventional compounding/masterbatching techniques.
  • the present dyes generally dissolve or disperse readily in hot plastics melt and provide bright coloration generally with good clarity and good light fastness.
  • plastics materials when coloured with the above dyes form a further feature of the present invention.
  • the compounds of Formulae (1) and (2) may be obtained by usual methods for the preparation of anthraquinone compounds such as by oxidation of anthracene or substituted anthracenes with potassium dichromate in sulphuric acid or by reaction of phthalic anhydride with benzene or a substituted benzene in the presence of aluminium chloride followed by ring closure in hot sulphuric acid.
  • Fluorosulphonyl groups may be introduced into the compound of Formula (1) or (2) by methods generally available in the literature. For example reaction of such a precursor of a compound of Formulae (1) or (2) free from fluorosulphonyl with chlorosulphonic acid optionally in the presence of dimethylformamide and thionylchloride at a temperature of from 30°C to 100°C gives the chlorosulphonyl derivative. The chlorosulphonyl derivative may be reacted in boiling aqueous media with potassium fluoride to give the fluorosulphonyl derivative.
  • a precursor compound of Formula (1) or (2) free from fluorosulphonyl may be sulphonated with sulphuric acid or oleum to give the sulphonic acid derivative which may be converted to the chlorosulphonyl derivative by reaction, either of the free acid or an inorganic salt thereof, with thionylchloride optionally in the presence of a chlorophosphorus compound such as phosphorus oxychloride or phosphorus pentachloride in an organic liquid such as an aromatic hydrocarbon at a temperature of from 20°C to 110°C.
  • the chlorosulphonyl derivative may then be converted to the fluorosulphonyl derivative as described above.
  • the compounds of Formulae (1) and (2) are useful for the coloration of synthetic textile materials particularly polyester textile materials and fibre blends thereof to which they impart colours which have excellent wet and light fastness properties.
  • the compounds of Formulae (1) and (2) are also useful for the mass coloration of plastics as described above and impart bright colours generally with good clarity and light fastness.
  • the sulphonyl chloride derivative (0.6 parts) was added to 1, 4-dioxane (94 parts) at room temperature before adding potassium fluoride (5.2 parts) in water (111 parts). After heating at 60°C for 4 hours the mixture was cooled, filtered and dried to yield 1,5-dihydroxy-2-(4'-hydroxy-3'-fluorosulphonylphenyl -4,8-diaminoanthraquinone (1.02 parts).
  • ⁇ MAX 587nm, 629 nm.
  • the dye of Formula (2) above was also prepared by the procedure of Example 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
EP95907057A 1994-02-10 1995-01-23 Anthraquinone dyes containing a fluorosulphonyl group and use thereof Expired - Lifetime EP0743994B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9402607A GB9402607D0 (en) 1994-02-10 1994-02-10 Process
GB9402607 1994-02-10
PCT/GB1995/000097 WO1995021958A1 (en) 1994-02-10 1995-01-23 Anthraquinone dyes containing a fluorosulphonyl group and use thereof

Publications (2)

Publication Number Publication Date
EP0743994A1 EP0743994A1 (en) 1996-11-27
EP0743994B1 true EP0743994B1 (en) 2002-04-17

Family

ID=10750203

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95907057A Expired - Lifetime EP0743994B1 (en) 1994-02-10 1995-01-23 Anthraquinone dyes containing a fluorosulphonyl group and use thereof

Country Status (14)

Country Link
US (1) US5759211A (enrdf_load_stackoverflow)
EP (1) EP0743994B1 (enrdf_load_stackoverflow)
JP (1) JP3893149B2 (enrdf_load_stackoverflow)
KR (1) KR970701284A (enrdf_load_stackoverflow)
AU (1) AU1540095A (enrdf_load_stackoverflow)
CA (1) CA2180852A1 (enrdf_load_stackoverflow)
CO (1) CO4370117A1 (enrdf_load_stackoverflow)
DE (1) DE69526430T2 (enrdf_load_stackoverflow)
ES (1) ES2174924T3 (enrdf_load_stackoverflow)
GB (1) GB9402607D0 (enrdf_load_stackoverflow)
IN (1) IN190255B (enrdf_load_stackoverflow)
TW (1) TW306942B (enrdf_load_stackoverflow)
WO (1) WO1995021958A1 (enrdf_load_stackoverflow)
ZA (1) ZA95793B (enrdf_load_stackoverflow)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6140517A (en) * 1996-09-03 2000-10-31 Eastman Chemical Company Anthraquinone polysulfonamide colorants
GB0217487D0 (en) * 2002-07-29 2002-09-04 Dystar Textilfarben Gmbh & Co Non-azo disperse dye mixtures
EP1533105A1 (en) * 2003-10-15 2005-05-25 Orient Chemical Industries, Ltd. Laser-transmissible colored resin composition and method for laser welding
EP1820826A1 (en) * 2006-02-09 2007-08-22 DyStar Textilfarben GmbH & Co. Deutschland KG Dyestuffs and Hair Dye Compositions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2576037A (en) * 1947-08-25 1951-11-20 American Cyanamid Co Sulfonyl fluorides of amino azo dyestuffs
US3952029A (en) * 1975-01-13 1976-04-20 Eastman Kodak Company 2-(Fluorosulfonyl)ethylamino anthraquinones
JPS6024865B2 (ja) * 1977-09-27 1985-06-14 三菱化学株式会社 セルロ−ス含有材料の熱転写捺染法

Also Published As

Publication number Publication date
JPH09509200A (ja) 1997-09-16
CA2180852A1 (en) 1995-08-17
GB9402607D0 (en) 1994-04-06
US5759211A (en) 1998-06-02
DE69526430D1 (de) 2002-05-23
TW306942B (enrdf_load_stackoverflow) 1997-06-01
ZA95793B (en) 1996-08-12
IN190255B (enrdf_load_stackoverflow) 2003-07-05
KR970701284A (ko) 1997-03-17
DE69526430T2 (de) 2002-12-12
CO4370117A1 (es) 1996-10-07
JP3893149B2 (ja) 2007-03-14
AU1540095A (en) 1995-08-29
ES2174924T3 (es) 2002-11-16
EP0743994A1 (en) 1996-11-27
WO1995021958A1 (en) 1995-08-17

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